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  Home > JCE Print > Journal of Chemical Education > Issues > 1996  > December  >
In the Laboratory
The Microscale Laboratory
Microscale Synthesis and Electronic Absorption Spectroscopy of Tetraphenylporphyrin H2(TPP) and Metalloporphyrins ZnII(TPP) and NiII(TPP)
Diane Marsh
Department of Chemistry, Riverside Community College, Riverside, CA 92506

Larry Mink
Department of Chemistry, California State University, San Bernardino, CA 92407

Cover
December 1996
Vol. 73 No. 12
p. 1188
Abstract
The microscale syntheses of Tetraphenylporphyrin, H2(TPP), and the corresponding metalloporphyrins ZnII(TPP) and NiII(TPP) are reported. H2(TPP) is synthesized by the condensation of benzaldehyde and pyrrole, and the subsequent metallation of H2(TPP) is achieved with anhydrous ZnIICl2 or NiIICl2 in DMF. The compounds are analyzed by their electronic absorption spectra in the visible region, and by their fluorescence properties. The visible spectra are obtained on a Spectronic 20 spectrophotometer. Analysis of the electronic absorption spectra is presented on the basis of ZnII(TPP) representing the class of regular metallporphyins, and NiII(TPP) representing the class of hypsoporphyrins. The hypsochromic (blue) shifts of the NiII(TPP) complex is discussed in terms of significant metal to ligand pi-backbonding. A group theoretical interpretation of the simplified electronic absorption spectra of the metalloporphyrins of D4h symmetry, relative to the free-base porphyrin H2(TPP) of D2h symmetry is offered.
More Information
*  Citation
 Marsh, Diane F.; Mink, Larry M. J. Chem. Educ. 1996 73 1188.
*  Keywords
 Laboratory Instruction
*  History
 Created:
Last Updated:		 August 5, 1999
February 21, 2006
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